Potassium Carbonate → HCID 57699599, compound

HRID 1011145Notes

Reaction equation

HRID 1011145 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C@@H:9]([O:13][C:14]1[NH:15][C:16]([NH2:25])=[C:17]2[C:21]([N:22]=1)=[N:20][C:19]([O:23][CH3:24])=[N:18]2)[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][CH:35]1[CH2:40][CH2:39][O:38][C:37]([CH3:42])([CH3:41])[CH2:36]1>CN(C=O)C>[CH3:41][C:37]1([CH3:42])[CH2:36][CH:35]([CH2:34][CH2:33][N:20]2[C:19]([O:23][CH3:24])=[N:18][C:17]3[C:21]2=[N:22][C:14]([O:13][C@H:9]([CH3:8])[CH2:10][CH2:11][CH3:12])=[N:15][C:16]=3[NH2:25])[CH2:40][CH2:39][O:38]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 576997121050496-83-72×HCID 178448284HCID 178448284, compound

Product 1

HCID 57699599HCID 57699599, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-{[(1R)-1-Methylbutyl]oxy}-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (100 mg, 0.274 mmol) was heated with potassium carbonate (37.8 mg, 0.274 mmol) in dry DMF (2 ml) at 60° C. under nitrogen for 1 hour and then cooled to room temperature. 4-(2-Bromoethyl)-2,2-dimethyltetrahydro-2H-pyran (72.6 mg, 0.328 mmol) was added and the reaction mixture heated at 50° C., for 16 hours. LCMS indicated the reaction to be incomplete and more 4-(2-bromoethyl)-2,2-dimethyltetrahydro-2H-pyran (35 mg) was added, and the reaction stirred at 50° C. for a further 5 hours and then partitioned between water (2 ml) and DCM (5 ml). The aqueous layer was further extracted with DCM (2×5 ml). The combined organic layers were combined and dried by passing through a hydrophobic frit and then evaporated to dryness using a nitrogen blowdown unit. The residue was dissolved in methanol (0.6 ml) and purified by mass directed autopreparation. Evaporation of the product containing fractions under a stream of nitrogen in a blowdown apparatus gave the title compound as a white solid (92 mg).

Workup

  1. temperaturethe reaction mixture heated at 50° C., for 16 hours
  2. customthe reaction
  3. custompartitioned between water (2 ml) and DCM (5 ml)
  4. extractionThe aqueous layer was further extracted with DCM (2×5 ml)
  5. customdried
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in methanol (0.6 ml)
  8. custompurified by mass
  9. customEvaporation of the product
  10. additioncontaining fractions under a stream of nitrogen in a blowdown apparatus

Sources & evidence

ORD record
ord-24538bed7f8f46ac84fed2321516cafc
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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